Technology Process of Benzoic acid 2-[(3aS,5R,6R,6aS)-6-formyl-5-(tetrahydro-pyran-2-yloxy)-1,3a,4,5,6,6a-hexahydro-pentalen-2-yl]-ethyl ester
There total 23 articles about Benzoic acid 2-[(3aS,5R,6R,6aS)-6-formyl-5-(tetrahydro-pyran-2-yloxy)-1,3a,4,5,6,6a-hexahydro-pentalen-2-yl]-ethyl ester which
guide to synthetic route it.
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synthetic route:
- Guidance literature:
-
Multi-step reaction with 9 steps
1: 4.03 g / p-TsOH / acetone; H2O / 2 h / 40 °C
2: 7.25 g / p-TsOH / CH2Cl2 / 0.5 h / Ambient temperature
3: 86.2 g / tetrahydrofuran; dimethylformamide / 4 h / 20 - 30 °C
4: lithium dicyclohexylamide / hexamethylphosphoric acid triamide; tetrahydrofuran / 0.33 h / -73 - -65 °C
5: LiAlH4, NaOH (4percent) / diethyl ether / 0.5 h / 5 - 10 °C
6: pyridine / 0.25 h / 20 - 30 °C
7: 12.6 g / p-TsOH / H2O; methanol / 1.5 h
9: 3.10 g / pyridine-SO3, Et3N / dimethylsulfoxide / 1 h / Ambient temperature
With
sodium hydroxide; lithium aluminium tetrahydride; sulfur trioxide pyridine complex; lithium dicyclohexylamide; toluene-4-sulfonic acid; triethylamine;
In
tetrahydrofuran; pyridine; methanol; N,N,N,N,N,N-hexamethylphosphoric triamide; diethyl ether; dichloromethane; water; dimethyl sulfoxide; N,N-dimethyl-formamide; acetone;
DOI:10.1248/cpb.35.4000
- Guidance literature:
-
Multi-step reaction with 8 steps
1: 960 g / p-TsOH / CH2Cl2 / 0.5 h
2: 61 percent / 1.) lithium dicyclohexylamide / 1.) THF, -78 deg C, 1 h; 2.) HMPA, 45 min
3: 1.) NaH / 1.) THF, DMF, HMPA, 30 min; 2.) THF, room temp., 3 h
4: 52 mg / Raney Ni / ethanol / 1 h / Heating
5: 45 mg / LiAlH4 / tetrahydrofuran / 0.5 h
6: 32 mg / pyridine / 1 h / Ambient temperature
7: 18 mg / Bu4NF (1M) / tetrahydrofuran / 7 h / Ambient temperature
8: 3.10 g / pyridine-SO3, Et3N / dimethylsulfoxide / 1 h / Ambient temperature
With
lithium aluminium tetrahydride; tetrabutyl ammonium fluoride; sulfur trioxide pyridine complex; sodium hydride; lithium dicyclohexylamide; toluene-4-sulfonic acid; triethylamine;
nickel;
In
tetrahydrofuran; pyridine; ethanol; dichloromethane; dimethyl sulfoxide;
DOI:10.1248/cpb.35.4000
- Guidance literature:
-
Multi-step reaction with 8 steps
1: 960 g / p-TsOH / CH2Cl2 / 0.5 h
2: 61 percent / 1.) lithium dicyclohexylamide / 1.) THF, -78 deg C, 1 h; 2.) HMPA, 45 min
3: 1.) NaH / 1.) THF, DMF, HMPA, 30 min; 2.) THF, room temp., 3 h
4: 52 mg / Raney Ni / ethanol / 1 h / Heating
5: 45 mg / LiAlH4 / tetrahydrofuran / 0.5 h
6: 32 mg / pyridine / 1 h / Ambient temperature
7: 18 mg / Bu4NF (1M) / tetrahydrofuran / 7 h / Ambient temperature
8: 3.10 g / pyridine-SO3, Et3N / dimethylsulfoxide / 1 h / Ambient temperature
With
lithium aluminium tetrahydride; tetrabutyl ammonium fluoride; sulfur trioxide pyridine complex; sodium hydride; lithium dicyclohexylamide; toluene-4-sulfonic acid; triethylamine;
nickel;
In
tetrahydrofuran; pyridine; ethanol; dichloromethane; dimethyl sulfoxide;
DOI:10.1248/cpb.35.4000
